881674-06-2

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl ester is used as a building block for the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties, potentially targeting a range of diseases and conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl ester serves as a versatile intermediate for the creation of various organic compounds. Its reactivity and functional groups enable chemists to synthesize a wide array of molecules with tailored properties for use in different applications.
Used in Research and Development:
This pyrrole derivative is also utilized in research and development settings to explore its chemical behavior and potential applications. Its unique structure and properties make it an interesting subject for further investigation, which could lead to the discovery of new uses and applications in various industries.

Upstream product

• 445-27-2 2'-Fluoroacetophenone 
• 881673-98-9 ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate 
• 881674-01-7 ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate 
• 105-56-6 ethyl 2-cyanoacetate 
• 655-15-2 2-bromo-2'-fluoroacetophenone 

Downstream Products

• 2098974-13-9 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrole-3-yl]-N-methylmethylamine fumaric acid salt 
• 881681-00-1 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine 
• 881674-56-2 5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde 
• 881677-11-8 5‐(2-fluorophenyl)‐1‐(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde 
• 881677-02-7 5-(2-fluorophenyl)-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde 
• 881677-04-9 1-{[3-(ethylsulfonyl)phenyl]sulfonyl}-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde 
• 881677-06-1 2-{[2-(2-fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile 
• 881677-08-3 4-{[2-(2-fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile 
• 881677-09-4 5-(2-fluorophenyl)-1-[(2-fluorophenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde 
• 1883595-39-8 C₁₇H₁₄FN₃O₃S 
• 1883595-37-6 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carboxylic acid 

Relevant academic research and scientific papers

Identification of a novel fluoropyrrole derivative as a potassium-competitive acid blocker with long duration of action

With the aim to find a novel long-lasting potassium-competitive acid blocker (P-CAB) that would perfectly overcome the limitations of proton pump inhibitors (PPIs), we tried various approaches based on pyrrole derivative 1b as a lead compound. As part of

Preparation method of drug for treating gastric acid related diseases

The invention discloses a preparation method of a drug TAK438 for treating gastric acid related diseases. According to the preparation method, 2-bromo-2'-fluoroacetophenone is taken as the primary raw material, and the target product TAK438 is obtained through the following reactions: condensation reaction, cyclization reaction, reduction reaction, sulfonylation reaction, and reductive amination reaction. The preparation method has the advantages of easily-available raw material, easy control, and high yield, and can be applied to industrial production.

Proton pump inhibitors

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3- ylsulfonyl)-1 H -pyrrol-3-yl]- n -methylmethanamine fumarate (tak-438) as a Potassium-Competitive Acid Blocker (P-CAB)

In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log"‰D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H +,K+-ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)- 1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.

Acid secretion inhibitor

The present invention provides a compound having a superior acid secretion inhibitory effect and showing an antiulcer activity and the like. The present invention provides a compound represented by the formula (I) wherein R1 is a nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle, the nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle optionally has substituent(s), R2 is an optionally substituted C6-14 aryl group, an optionally substituted thienyl group or an optionally substituted pyridyl group, R3 and R4 are each a hydrogen atom, or one of R3 and R4 is a hydrogen atom and the other is an optionally substituted lower alkyl group, an acyl group, a halogen atom, a cyano group or a nitro group, and R5 is an alkyl group or a salt thereof.

PROTON PUMP INHIBITORS

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R2, R3 and R4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R5 and R6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

PROTON PUMP INHIBITORS

Proton pump inhibitors which have excellent proton pumping activity and which can be converted in vivo into proton pump inhibitors to exhibit antiulcer effect and so on, containing compounds represented by the general formula (I) or salts thereof or prodrugs of the same: (I) wherein X and Y are each independently a free valency or a spacer whose main chain has 1 to 20 carbon atoms; R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; R2, R3 and R4 are each independently hydrogen, an optionally substituted hydrocarbon group, optionally substituted thienyl, optionally substituted benzo[b]thienyl, optionally substituted furyl, optionally substituted pyridyl, optionally substituted pyrazolyl, optionally substituted pyrimidinyl, acyl, halogeno, cyano, or nitro; and R5 and R6 are each independently hydrogen or an optionally substituted hydrocarbon group.